Potassium Carbonate → (3R*,4R*)-1-[(1-acetylpiperidin-4-yl)carbonyl]-3-(3,4-dichlorophenyl)-N-methylpiperidin-4-amine

HRID 2047436노트

반응식

HRID 2047436 반응식
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]([N:12]2[CH2:17][CH2:16][C@@H:15]([N:18](C)[C:19](=O)C(F)(F)F)[C@H:14]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=3)[CH2:13]2)=[O:11])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CO.O>[C:1]([N:4]1[CH2:5][CH2:6][CH:7]([C:10]([N:12]2[CH2:17][CH2:16][C@@H:15]([NH:18][CH3:19])[C@H:14]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=3)[CH2:13]2)=[O:11])[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

참가 물질

5

반응물 2

HCID 11430Potassium Carbonate2회HCID 57741667rel-N-[(3R,4R)-1-[(1-Acetyl-4-piperidinyl)carbonyl]-3-(3,4-dichlorophenyl)-4-piperidinyl]-2,2,2-trifluoro-N-methylacetamide

생성물 1

HCID 57741761(3R*,4R*)-1-[(1-acetylpiperidin-4-yl)carbonyl]-3-(3,4-dichlorophenyl)-N-methylpiperidin-4-amine수율 58%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

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온도
50 °C

실험 절차

To a mixed solution of the compound (0.66 g) obtained in step 4 in methanol (6.5 mL) and water (1.3 mL) was added potassium carbonate (0.35 g) at room temperature, and the mixture was stirred at 50° C. for 24 hr. Furthermore, potassium carbonate (1.70 g) was added, and the mixture was stirred at 50° C. for 6 days. The organic solvent was evaporated under reduced pressure, and the residue was poured into saturated aqueous sodium hydrogen carbonate solution and ethyl acetate. The organic layer was washed with saturated brine and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (NH Chromatorex) (solvent gradient; 0→9% methanol/ethyl acetate) to give the title compound (0.30 g, 58%) as a white amorphous solid.

후처리

  1. stirringthe mixture was stirred at 50° C. for 6 days
  2. customThe organic solvent was evaporated under reduced pressure
  3. additionthe residue was poured into saturated aqueous sodium hydrogen carbonate solution and ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. customdried
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (NH Chromatorex) (solvent gradient; 0→9% methanol/ethyl acetate)

출처 및 근거

ORD 기록
ord-ad22189badbd4a01841e7b78669e3d23
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08592454B2

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